WHERE'S YOUR SKIN IN THE GAME?

Preserving generational wealth is never accidental.

3 out of 4 family offices fail to reach the second generation, and 9 out of 10 don’t make it to the third.

That’s not bad luck—it’s structural failure.

But here’s the issue:

The logic behind how skin in the game is evaluated often breaks down.

There are 4 places where the thinking falls apart—not just in theory, but in practice.

1. Double Standards

Most investors we meet who demand skin in the game don’t apply that logic consistently.

They allocate to public companies where executives hold no equity, and to $100M+ funds with zero GP capital committed. We’ve even seen fund managers require co-investment—despite having no personal capital committed to their own funds.

Other allocators hold positions in blind pools deployed by analysts they’ve never met, and run by C-suites with no skin in the game, just large salaries and upside sharing.

Yet, these allocations are all made based on track record and potential upside alone.

And the logic behind co-investment as “skin in the game” often assumes a yield-driven risk profile—where debt, timing, and income drive outcomes. In that model, assets behave like commodity real estate, reacting to macro cycles and introducing the very volatility most investors aim to avoid.

But when you strip those risks out—no debt, no reliance on yield for valuation—the logic starts to shift.

It’s not a rejection of the principles.
It’s a more complete expression of them.

If you already believe in staying low leverage, why not own assets that don’t need any at all?

If you want durable value, why not focus on assets that appreciate without engineered revenue?

That’s not a different philosophy.
It’s just a more disciplined version of the one you already have.

So I’m not saying that co-investment is flawed.

But applying that logic to a model with stronger fundamentals—and ignoring the double standard with private real estate—is.

2. Capital Aggregator ≠ Operator

There’s also a difference between capital aggregators (like many syndicators) and real operators.

If someone is raising capital but outsources the entire deal’s execution to a third-party manager—fine. The co-investment should be significant.

I’d even go as far to say that their level of investment should far exceed what they earn from fees on the hold.

But when you’re dealing with a real operating sponsor, they’re already all in.

Time, reputation, infrastructure—that is real skin in the game.

When the value comes from execution, alignment isn’t optional. It’s structural.

And by cutting out intermediaries and vanity co-investments, all parties can often get sharper economics and stronger alignment on opportunities.

3. Transaction ≠ Partnership

Too much capital is deployed into transactions.

Not partnerships.

The best partnerships aren’t built on short-term projections, or what was returned on the latest milestone.

They’re about trust, alignment, and shared ambition—the real foundation of generational wealth.

4. Capital ≠ Conviction

What it takes to build wealth is often aligned with what it takes to preserve it.

More often than not, they go hand in hand.

But sometimes, they’re in tension.

And when an investor fixates on modeled downside, at the expense of understanding the character of the deal itself, they miss the whole point.

Not all asset classes are created equal.

Each asset class carries its own operational profile.

A multifamily, office, self-storage, or single family rental deal doesn’t require the same operational lift a boutique hotel, or a luxury short-term rental. And without accounting for differences in complexity, volatility, or daily involvement—that’s not alignment. That’s misapplied convention.

Take luxury SFL:
Onsite operations are far simpler than most traditional CRE.
But revenue operations? Far more demanding.

It’s the inverse of most models—where asset management is heavy, but income is passive and contractual.

With SFL, physical ops are light.
But performance depends on how well you operate revenue.

And that’s the edge:
Even at 60% of projected income, a luxury SFL asset can still cash flow positively.
In traditional CRE, even boutique hotels with too much debt, a 60% occupancy isn’t a dip. It’s a disaster.

Risk can be managed.

But conviction can’t be spreadsheeted.

And capital that’s overly fixated on co-investment optics doesn’t strengthen the deal—it drags on it.

I don’t believe capital is the only (or even the best) way to demonstrate conviction in a potential deal or partnership.

Because capital only performs when paired with execution.

We’ve spent years building trust, credibility, and a track record that stands on its own. Every investment puts our name, time, and expertise on the line.

We’re all in.

And opportunity cost is real.

That’s why we’re highly selective about the properties we take on—and the partners we work with.

We focus on alignment where it really matters:

a) The quality of the deals we take on

b) The results we deliver through disciplined execution

c) The quality and resiliency of the properties themselves

Many CRE models cracked under this last economic cycle.

4 out of 5 asset classes in the NPI have been in the negative since the COVID pandemic.

Yet throughout that same period—before, during, and after the downturn—luxury SFL assets under our stewardship didn’t just hold their value; they thrived.

Luxury SFL has proven to be one of the most resilient real estate asset classes, offering a natural hedge against volatility in other commercial real estate sectors.

Truly exceptional and well maintained properties benefit from greatly accelerated CAGRs that operate independently of yield, creating risk-adjusted returns that most traditional real estate investments can’t match.

But what sets our deals apart isn’t just the strength of the asset class—it’s how we structure them.

Our model is built to hold and operate exceptional properties—indefinitely.

The best returns don’t come from cycling in and out of commoditized deals, or losing gains to taxes and time between trades.

Our partners prioritize:

• simplicity

• generational wealth

• tax efficiency

• maximizing the compounding effect over time

• the flexibility to choose their deals, and

• the ability to deploy more capital into a strong pipeline of high-value opportunities

Jack Laurier is not a blind pool.

Each asset is structured as a standalone investment with full transparency and operational control. We partner with a select group of aligned capital—offering deal-by-deal flexibility within a unified vehicle that benefits from shared infrastructure, aligned incentives, and efficient capital deployment.

By cutting out intermediaries to create sharper economics and stronger alignment, our partners can invest in high-performing, risk-adjusted luxury vacation rental deals—without the constraints of traditional pooled real estate investments.

We do well only when our properties generate cash profits and grow, keeping our focus on asset-level value creation rather than constant fundraising

We eliminate early downside risk by avoiding debt until stabilization. Each asset stands on its own fundamentals—not financial engineering.

Strategic recapitalization (no fees on refinancing) lets us accelerate IRR and enhance returns without increasing risk.

The result: true alignment, and disciplined execution at every stage.

This conservative structure, paired with the resilience of the asset class, creates a level of security that is truly rare in private equity real estate.

2025 marks 16 years in luxury real estate and vacation rentals for me, with experience spanning nearly every vertical in the space—from platforms and advisory to operations, asset management, marketing, and acquisitions.

Assets under our stewardship have achieved Gross Rent Multipliers as low as 4x, Gross Margins above 50%, and double-digit cash yields.

If we just consider the 4 most recent luxury properties we’ve taken on:

4 different properties, 4 different countries, 4 distinct markets.

Each ranked in the top 1% of highest-grossing homes in its region.

The odds of that happening by chance?
1% × 1% × 1% × 1%—a vanishingly small probability that it’s luck.

I can say with conviction: we know how to replicate success.

Our proven marketing and asset management frameworks deliver a return profile that few can match.

They’re predictable, repeatable, and they work because they’re built on timeless principles of luxury real estate.

But these aren’t isolated results.

Our team has 25+ years of combined experience, operating over $150M in luxury SFL real estate, spanning 36 markets throughout the Americas, Caribbean, Europe, and Southeast Asia—building deep expertise in every phase of the luxury SFL investment cycle

The difference is discipline—applied globally, executed locally.

That’s the advantage we bring, and where others fall short.

We’re not interested in working around property defects, extended maintenance delays, or uninspired assets. 

And we’re not going to market properties that lack vision or waste time debating over essential value-add improvements in building systems, design, FF&E, or OS&E.

In our world, there’s no value in half-measures.

We require a base fee and minimum CAPEX in every deal. Anything less compromises execution with disproportionate risk, and we don’t operate that way.

We focus on exceptional properties—those that deliver enriching, memorable experiences to even the most discerning guests.

Rare, beautifully crafted spaces in picturesque settings, filled with gratified guests who are willing—and happy—to pay market-leading ADRs.

We work with partners who understand that.

Who see that quality deal flow and a proven track record matter more than performative co-investment optics.

Who recognize that that selecting the right asset is as critical as the deal itself.

And who value aligning early with a team built for the long game—disciplined, experienced, and thinking decades ahead.